CA1243327A - Preparation of 6-carboxy-3, 4-dihydro-2h-pyran - Google Patents
Preparation of 6-carboxy-3, 4-dihydro-2h-pyranInfo
- Publication number
- CA1243327A CA1243327A CA000442362A CA442362A CA1243327A CA 1243327 A CA1243327 A CA 1243327A CA 000442362 A CA000442362 A CA 000442362A CA 442362 A CA442362 A CA 442362A CA 1243327 A CA1243327 A CA 1243327A
- Authority
- CA
- Canada
- Prior art keywords
- dihydro
- carboxy
- hydrogen
- pyran
- inorganic base
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- OXUPSEKWDOSMIN-UHFFFAOYSA-N 3,4-dihydro-2h-pyran-6-carboxylic acid Chemical compound OC(=O)C1=CCCCO1 OXUPSEKWDOSMIN-UHFFFAOYSA-N 0.000 title abstract description 17
- 238000002360 preparation method Methods 0.000 title description 3
- -1 1,4-disubstituted butane Chemical class 0.000 claims abstract description 20
- 229910052751 metal Inorganic materials 0.000 claims abstract description 12
- 239000002184 metal Substances 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 11
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 8
- 150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 6
- 230000003197 catalytic effect Effects 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 22
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 229910001868 water Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- MQIKJSYMMJWAMP-UHFFFAOYSA-N dicobalt octacarbonyl Chemical group [Co+2].[Co+2].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] MQIKJSYMMJWAMP-UHFFFAOYSA-N 0.000 claims description 4
- BRYRYYVVJRQURH-UHFFFAOYSA-N 2-methyl-3,4-dihydro-2h-pyran-6-carboxylic acid Chemical compound CC1CCC=C(C(O)=O)O1 BRYRYYVVJRQURH-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 10
- 239000000376 reactant Substances 0.000 description 7
- 229960004132 diethyl ether Drugs 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 235000011116 calcium hydroxide Nutrition 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- 238000005810 carbonylation reaction Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QDLTWESUVICXFC-UHFFFAOYSA-N 1,4-dibromo-2,2-dimethylbutane Chemical compound BrCC(C)(C)CCBr QDLTWESUVICXFC-UHFFFAOYSA-N 0.000 description 2
- SBCDMKDTWODACO-UHFFFAOYSA-N 1,4-dibromo-2-methylbutane Chemical compound BrCC(C)CCBr SBCDMKDTWODACO-UHFFFAOYSA-N 0.000 description 2
- ZMXREKVNGMXQND-UHFFFAOYSA-N 1,4-dibromobutan-2-ylbenzene Chemical compound BrCCC(CBr)C1=CC=CC=C1 ZMXREKVNGMXQND-UHFFFAOYSA-N 0.000 description 2
- CNBFRBXEGGRSPL-UHFFFAOYSA-N 1,4-dibromopentane Chemical compound CC(Br)CCCBr CNBFRBXEGGRSPL-UHFFFAOYSA-N 0.000 description 2
- MQYLGFBWOZXHHF-UHFFFAOYSA-N 2,5-dibromohexane Chemical compound CC(Br)CCC(C)Br MQYLGFBWOZXHHF-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229910021012 Co2(CO)8 Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- STFHKSYRFIGDIE-UHFFFAOYSA-N 1,4-dibromo-2,3-dimethylbutane Chemical compound BrCC(C)C(C)CBr STFHKSYRFIGDIE-UHFFFAOYSA-N 0.000 description 1
- CSRGCRJFPFKJOY-UHFFFAOYSA-N 1,4-dibromo-2,3-dimethylpentane Chemical compound CC(Br)C(C)C(C)CBr CSRGCRJFPFKJOY-UHFFFAOYSA-N 0.000 description 1
- LWBXRVWHKDVRTQ-UHFFFAOYSA-N 1,4-dibromo-3-methylpentane Chemical compound CC(Br)C(C)CCBr LWBXRVWHKDVRTQ-UHFFFAOYSA-N 0.000 description 1
- LCDAQRPVXAOTAE-UHFFFAOYSA-N 1-(1,4-dibromobutan-2-yl)-4-ethylbenzene Chemical compound CCC1=CC=C(C(CBr)CCBr)C=C1 LCDAQRPVXAOTAE-UHFFFAOYSA-N 0.000 description 1
- VGQCMDVBYCTRPJ-UHFFFAOYSA-N 1-(1,4-dibromobutan-2-yl)-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(C(CBr)CCBr)C=C1 VGQCMDVBYCTRPJ-UHFFFAOYSA-N 0.000 description 1
- NIDSRGCVYOEDFW-UHFFFAOYSA-N 1-bromo-4-chlorobutane Chemical compound ClCCCCBr NIDSRGCVYOEDFW-UHFFFAOYSA-N 0.000 description 1
- IMVNDNQARZYRBS-UHFFFAOYSA-N 2,3,4-trimethyl-3,4-dihydro-2h-pyran-6-carboxylic acid Chemical compound CC1OC(C(O)=O)=CC(C)C1C IMVNDNQARZYRBS-UHFFFAOYSA-N 0.000 description 1
- PHMXXMFOSQBXNV-UHFFFAOYSA-N 2,3-dichlorooxane Chemical compound ClC1CCCOC1Cl PHMXXMFOSQBXNV-UHFFFAOYSA-N 0.000 description 1
- ZXTHWIZHGLNEPG-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1 ZXTHWIZHGLNEPG-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- QOCMTLDZJBVTEA-UHFFFAOYSA-N 3,3-dimethyl-2,4-dihydropyran-6-carboxylic acid Chemical compound CC1(C)COC(C(O)=O)=CC1 QOCMTLDZJBVTEA-UHFFFAOYSA-N 0.000 description 1
- XFTCGWLUGNBFJC-UHFFFAOYSA-N 3,4-dimethyl-3,4-dihydro-2h-pyran-6-carboxylic acid Chemical compound CC1COC(C(O)=O)=CC1C XFTCGWLUGNBFJC-UHFFFAOYSA-N 0.000 description 1
- GJYYUTBMUNNEOF-UHFFFAOYSA-N 3-chlorooxane-2-carbonitrile Chemical compound ClC1CCCOC1C#N GJYYUTBMUNNEOF-UHFFFAOYSA-N 0.000 description 1
- CEMUTYUYORXOFL-UHFFFAOYSA-N 3-methyl-3,4-dihydro-2h-pyran-6-carboxylic acid Chemical compound CC1COC(C(O)=O)=CC1 CEMUTYUYORXOFL-UHFFFAOYSA-N 0.000 description 1
- UWGJXAPAGPRICG-UHFFFAOYSA-N 3-phenyl-3,4-dihydro-2h-pyran-6-carboxylic acid Chemical compound C1OC(C(=O)O)=CCC1C1=CC=CC=C1 UWGJXAPAGPRICG-UHFFFAOYSA-N 0.000 description 1
- DUERZAXUGMIVFL-UHFFFAOYSA-N 4,4-dimethyl-2,3-dihydropyran-6-carboxylic acid Chemical compound CC1(C)CCOC(C(O)=O)=C1 DUERZAXUGMIVFL-UHFFFAOYSA-N 0.000 description 1
- GOXKPDHFLCKZMC-UHFFFAOYSA-N 4-(4-ethylphenyl)-3,4-dihydro-2h-pyran-6-carboxylic acid Chemical compound C1=CC(CC)=CC=C1C1C=C(C(O)=O)OCC1 GOXKPDHFLCKZMC-UHFFFAOYSA-N 0.000 description 1
- XMMGXTGFQKCEEZ-UHFFFAOYSA-N 4-(4-propan-2-ylphenyl)-3,4-dihydro-2h-pyran-6-carboxylic acid Chemical compound C1=CC(C(C)C)=CC=C1C1C=C(C(O)=O)OCC1 XMMGXTGFQKCEEZ-UHFFFAOYSA-N 0.000 description 1
- JUVKIOLTVFBWAT-UHFFFAOYSA-N 4-methyl-3,4-dihydro-2h-pyran-6-carboxylic acid Chemical compound CC1CCOC(C(O)=O)=C1 JUVKIOLTVFBWAT-UHFFFAOYSA-N 0.000 description 1
- ZYFFZEUTTRYCGZ-UHFFFAOYSA-N 4-phenyl-3,4-dihydro-2h-pyran-6-carboxylic acid Chemical compound C1COC(C(=O)O)=CC1C1=CC=CC=C1 ZYFFZEUTTRYCGZ-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101100401686 Schizosaccharomyces pombe (strain 972 / ATCC 24843) mis19 gene Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- VNWKTOKETHGBQD-AKLPVKDBSA-N carbane Chemical group [15CH4] VNWKTOKETHGBQD-AKLPVKDBSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 235000012254 magnesium hydroxide Nutrition 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54439983A | 1983-10-21 | 1983-10-21 | |
| US544,399 | 1983-10-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1243327A true CA1243327A (en) | 1988-10-18 |
Family
ID=24172012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000442362A Expired CA1243327A (en) | 1983-10-21 | 1983-12-01 | Preparation of 6-carboxy-3, 4-dihydro-2h-pyran |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0159993A4 (enrdf_load_stackoverflow) |
| JP (1) | JPS60501757A (enrdf_load_stackoverflow) |
| CA (1) | CA1243327A (enrdf_load_stackoverflow) |
| WO (1) | WO1985001731A1 (enrdf_load_stackoverflow) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4120874A (en) * | 1977-01-05 | 1978-10-17 | Monsanto Company | Diesters of 6-cyano-2,2-tetrahydropyrandicarboxylates |
-
1983
- 1983-11-15 EP EP19840900419 patent/EP0159993A4/en not_active Withdrawn
- 1983-11-15 WO PCT/US1983/001799 patent/WO1985001731A1/en not_active Application Discontinuation
- 1983-11-15 JP JP84500166A patent/JPS60501757A/ja active Granted
- 1983-12-01 CA CA000442362A patent/CA1243327A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| WO1985001731A1 (en) | 1985-04-25 |
| JPS60501757A (ja) | 1985-10-17 |
| EP0159993A4 (en) | 1987-01-20 |
| JPS6220188B2 (enrdf_load_stackoverflow) | 1987-05-06 |
| EP0159993A1 (en) | 1985-11-06 |
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